Startups & Venture · August 2026

“it shouldn't be about who has the best agent or who sounds the most shiny on paper, but really who has the data and the experience to demonstrate that they can do the work that's required.” — Hayden Brown, Masters of Scale

Hayden Brown arguing that Upwork's edge in the AI era is verified work-history data, not flashy self-presentation or AI-generated applications. She frames this as a meritocratic counterpoint to AI-inflated resumes and proposals.

Masters of Scale · 2026-08-18 Listen to the episode → More from Hayden Brown →

Transcript

Masters of Scale Around 11:55 into the episode
Hayden Brown

I mean, these are the big questions, and they're the right ones because we are seeing, you know, spam job proposals and applications. We really just want to put people's own interests. And needs on steroids, and then have that expressed through the hiring process and the recruitment process that we're supporting them with, including filtering out all of the AI kind of slop and noise that is creeping in now that these tools are so widespread.

Speaker 4

Right. I guess if I'm a job applicant, I guess I can create a lot of different versions of my application to a lot of different jobs that may or may not be right for me. And I may not even know what I'm doing. And I guess the same thing can happen on the other side about posting for jobs where if we can find a needle in the haystack, we'll do it, but otherwise we're just sort of testing the water.

Hayden Brown

Yeah. And I think that's one of the main values that we see being so enduring, even in the AI era for Upwork specifically and our customers is, you know, the problem we've always solved for them is giving them real, tangible, accurate data around who can do what. It's real data from our platform, observing people doing work and delivering for customers with dollars attached. So this is the most verified work history data really in the world, and it's at scale across 18 million freelancers that were active in the last year. This type of data is what then gives customers confidence in making that hire, not noise that was created by an AI agent applying for them, not these empty promises or claims about their expertise. It's actually stripping us back to like what does the data say in terms of who's good at what? And frankly, advancing this meritocratic idea of it shouldn't be about who has the best agent or who sounds the most shiny on paper, but really who has the data and the experience to demonstrate that they can do the work that's required.

Speaker 4

That in the trenches data Hayden cites illustrates how human in the loop is actually unfolding in an AI world. 23% of businesses moving work back to humans from AI. So how does Upwork engage with the big AI companies, including open source players in China? And what does it mean that freelancers with AI skills earn 34% more? We'll talk about that and more after the break. Stay with us.

Jeff Berman

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Bob Safian

The Wired Newsroom is known for award-winning reporting on how technology shapes our world. On Wired's Uncanny Valley, we take that curiosity even further. Each week, journalists from Wired break down the biggest stories in tech while speaking directly with the people building, challenging, and reshaping the future. Is the AI boom sustainable? How do you protect your privacy in an age of constant surveillance? Uncanny Valley tackles the questions driving today's tech debates and lighting up your group chats. Listen to new episodes every Thursday, wherever you get your podcasts.

Speaker names from our own diarization · position estimated from where the line sits in the episode

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